1-Ethynyl-4-pentylbenzene → 2,5-Dibromo-3-(4-pentylphenyl)ethynylthiophene

HRID 554879

Reaktionsgleichung

Reaktionsgleichung von HRID 554879
[Br:1][C:2]1[S:3][C:4]([Br:8])=[CH:5][C:6]=1I.[C:9]([C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:13][CH:12]=1)#[CH:10]>C(N(CC)CC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[Br:1][C:2]1[S:3][C:4]([Br:8])=[CH:5][C:6]=1[C:10]#[C:9][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:13][CH:12]=1

Komponenten

6

Edukt 2

HCID 27751311-Ethynyl-4-pentylbenzeneHCID 130111782,5-Dibromo-3-iodothiophene

Produkt 1

HCID 674613932,5-Dibromo-3-(4-pentylphenyl)ethynylthiophene

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 2,5-dibromo-3-iodothiophene (3.52 grams, 9.57 mmol) and 1-ethynyl-4-pentylbenzene (1.65 grams, 9.57 mmol) in triethylamine (50 milliliters) were added dichlorobis(triphenylphosphine)palladium (II) (0.28 gram, 0.4 mmol) and copper(I) iodide (38 milligrams, 0.2 mmol) at 0° C. under argon. The resulting reaction mixture was stirred at 0° C. for 6 hours and at room temperature for 20 hours under argon. After evaporation of the solvent, the product obtained was purified by column chromatography on a silica gel using hexane as eluent. 2,5-Dibromo-3-(4-pentylphenyl)ethynylthiophene was obtained as a colorless liquid was. Yield: 3 grams (73 percent).

Aufarbeitung

  1. customThe resulting reaction mixture
  2. customAfter evaporation of the solvent
  3. customthe product obtained
  4. customwas purified by column chromatography on a silica gel

Quellen und Nachweise

ORD-Eintrag
ord-b02a38216ee44f9e9bba10618600342b
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08049205B2

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